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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
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Unavailable
Luxe
DAILY DROP
The Ritz-Carlton, Chicago
$417
95%
|
–
Magnificent Mile
was on HT
$645
Can’t-be-beat address on the Magnificent Mile (!).
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Unavailable
1 Room Left
Hip
21c Museum Hotel Chicago
$127
95%
|
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Downtown
was on HT
$161
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
Solid
DEAL
River Hotel
$129
86%
|
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Loop
was on HT
$153
Excellent authentic Italian resto onsite with fab deep dish pizza (natch).
Unavailable
Basic
DEAL
St. Clair Hotel - Magnificent Mile
$110
81%
|
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Downtown
was on HT
$284
Modern interiors within a cool old building, ideally situated in the heart of the city, steps from the Magnificent Mile.
Unavailable
Hip
The Allegro Royal Sonesta Hotel Chicago Loop
$179
90%
|
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Loop
A historic gem in the heart of Chicago’s downtown Theatre District, this boutique haven boasts lavish theatrics all its own with its elegant hobnobbing and glamour.
Unavailable
Basic
Level Chicago - River North
$189
94%
|
–
Downtown
You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.
Unavailable
Basic
Majestic Hotel
$108
84%
|
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Lakeview
was on HT
$141
On a quiet residential street, providing a relaxing respite in the bustling city.
Unavailable
Charming
Hotel Chicago West Loop
$136
81%
|
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West Loop
Fitness room is open 24/7, if all that museum-ing wasn’t enough of a workout for you.
Unavailable
Solid
DEAL
Club Quarters Hotel Wacker at Michigan, Chicago
$129
85%
|
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Loop
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
Basic
DEAL
Hampton Inn Chicago Orland Park
$114
90%
|
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West Side
Unavailable
Solid
The Royal Sonesta Chicago River North
$189
94%
|
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River North
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
Solid
Club Quarters Hotel Central Loop, Chicago
$144
85%
|
–
Loop
Chicago biggies like the Symphony Center & Willis Tower (skydeck is a must!) are within walking distance.
Unavailable
Hip
Ambassador Chicago
$189
92%
|
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Gold Coast
was on HT
$259
Sleek, modern and eclectic design welcomes the beautiful people. Now you can be one of them!
Unavailable
Hip
The Hoxton, Chicago
$297
95%
|
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West Loop
was on HT
$349
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
Unavailable
Luxe
DEAL
Pendry Chicago
$294
96%
|
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Loop
Bar Pendry's a loungey spot for a late-night glass of wine. Pro tip: seasonal rooftop bar's a must-do in the warmer months.
Unavailable
Solid
Holiday Inn Express & Suites CHICAGO - OAK FOREST
$109
–
North Side
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1 Room Left
Charming
DEAL
Wicker Park Inn
$195
94%
|
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Wicker Park
was on HT
$209
Drops ya in the heart of a vibrant, trendier-than-thou ‘hood teaming with vintage shopping, cool eateries & hoppin’ nightlife.
Unavailable
Solid
Level Chicago - Fulton Market
$225
86%
|
–
Downtown
was on HT
$273
The outdoor pool takes vacay vibes to new heights.
Unavailable
Luxe
Viceroy Chicago
$345
97%
|
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Gold Coast
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
Luxe
Loews Chicago Hotel
$259
96%
|
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Magnificent Mile
Head to the rooftop lounge for killer drinks and views (especially if it’s a Navy Pier fireworks night!).
Unavailable
Solid
DEAL
Hilton Garden Inn Chicago McCormick Place
$249
95%
|
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Loop
was on HT
$305
Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.
Unavailable
Luxe
The Blackstone, Autograph Collection
$279
90%
|
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Loop
There’s a reason it’s been voted one of the best hotels in the city – everything is top-notch, from the views, artwork & modern décor to the nostalgic cocktails.
Unavailable
1 Room Left
Solid
DEAL
LEVEL Chicago - Old Town
$208
88%
|
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Downtown
was on HT
$259
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
Basic
Holiday Inn Hotel & Suites Chicago Downtown
$166
82%
|
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Loop
was on HT
$187
Hit nearby Lou Mitchell’s for breakfast. It’s a Chicago institution and the starting point of Route 66.
Unavailable
Solid
Holiday Inn Express Chicago Magnificent Mile
$149
80%
|
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North Side
was on HT
$188
Free WiFi, so you can brag about your cool trip in real time.
Unavailable
Luxe
The Ritz-Carlton, Chicago
$595
95%
|
–
Magnificent Mile
was on HT
$645
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
3 Rooms Left
Solid
Riu Plaza Chicago
$175
–
Downtown
was on HT
$205
Relax, early riser. Breakfast included.
Unavailable
Luxe
Omni Chicago Hotel
$279
90%
|
–
Magnificent Mile
was on HT
$319
Ideal Mag Mile address just steps from endless shopping & world-class eateries.
Unavailable
Solid
Courtyard by Marriott Chicago at Medical District / UIC
$278
92%
|
–
Downtown
Spot-on location for all things medical campus – near UIC Chicago and Rush. PS: Little Italy dining nearby too(!).
Unavailable
Luxe
Waldorf Astoria Chicago
$656
96%
|
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Downtown
Guestrooms with kitted-out bathrooms (ft. a soaker tub + inset flat-screen, natch), wet bars & surround sound are a good time waiting to happen.
Unavailable
Solid
Residence Inn Chicago Downtown Magnificent Mile
$209
–
Downtown
was on HT
$219
Beautiful accommodations in the heart of the city, minutes from Navy Pier, downtown, Wrigley Field, you name it.
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Denver,
and tons more!